A buyer emailed me two listings last month and asked which one was the "real" Cupertino price. One was a condo near the Cupertino City Center area listed just under $800,000. The other was a single-family home a mile and a half away asking $3.5 million. Both were in Cupertino. Both were current. Neither was a mistake.
That gap is the story. If you've been watching Cupertino from outside the market, comparing it to Dublin, San Ramon, or Fremont on a single median-price line, you're comparing an average of two markets that don't behave the same way and increasingly don't sell to the same buyer.
The Number That Doesn't Add Up
Over the three months ending August 2026, Cupertino's median sale price came in around $2.9 million, down about 11 percent from the same period a year earlier. Read on its own, that looks like a market cooling off. But over that same window, the median price per square foot in Cupertino actually rose roughly 2.4 percent year over year.
Those two numbers cannot both mean the market is softening. A falling median alongside a rising price per square foot is usually a signal that the mix of what's selling has shifted, not that value is declining. Fewer of the largest, priciest single-family homes closed escrow during that stretch, and more of what did sell came from the smaller, lower-priced end of the market. The median moved because the sample moved, not because a given square foot of Cupertino got cheaper.
This matters if you're using Cupertino's median as a shorthand for "what does it cost to live here." It answers a different question: what happened to sell in the last 90 days.
Two Cupertinos, One Zip Code
Zoom into the neighborhood level and the split becomes obvious. In the Cupertino City Center micro-market, which sits closest to the old Vallco mall site, the median sale price over the three months ending February 2026 was around $785,000, down about 32 percent year over year. That's a small, condo-heavy pocket, and a handful of different transactions from one year to the next can swing a percentage like that, so I'd treat the exact figure as a signal of segment, not a precise trend line. But the direction it points is real: this is a fundamentally different price tier than the single-family stock that makes up most of the city.
That single-family stock, meanwhile, skews old. The median construction year across Cupertino is 1973, and close to 44 percent of homes were built between the 1940s and 1960s. When a handful of larger, updated homes on bigger lots trade in a given quarter, the citywide median jumps. When more condos and older, smaller homes trade, it drops. Neither move tells you that Cupertino got more or less expensive. It tells you which Cupertino sold that quarter.
For a buyer comparing this city to Danville or Pleasanton, the practical takeaway is to ask which Cupertino you're actually pricing against. A newer condo near City Center and a 1960s single-family home a mile north aren't the same product, and treating one citywide median as representative of both will throw off every comparison you make against another Bay Area suburb.
What "2,669 New Homes" Actually Means Right Now
Layered on top of that pricing split is a redevelopment story that's easy to misread if you only catch the headline. The Rise, the 50-acre project planned for the old Vallco mall site near the I-280 and Wolfe Road interchange, spent most of the last decade in legal and political limbo. That changed in 2026. After Sand Hill Property Company submitted a third modification application in November 2025, the City of Cupertino approved it on February 27, 2026, and the developer has targeted 2026 for the start of actual vertical construction, with the first residents potentially moving in as early as 2028.
That's real progress after years of the project existing mostly on paper. But two details in the 2026 filings change what this means for anyone shopping Cupertino today rather than in three years.
First, the mix shifted. The November 2025 modification reduced office and retail space and moved the balance of units toward market-rate housing and away from below-market-rate units, even as the total unit count held at roughly 2,669 homes across the full build-out. A city under pressure to deliver affordable housing lost some of that capacity on paper, even though the overall home count stayed the same headline number.
Second, and more relevant if you're deciding whether to wait this out, a fourth modification approved on August 24, 2026 dealt only with Blocks 1 and 2 of the project, refining parking, loading access, and building details for a combined 493 homes. That approval was explicitly described by the city as an implementation step ahead of future building-permit submittals, not a building permit itself. No pricing, HOA structure, or sales release timeline has been announced for any phase.
Put plainly: if you're weighing whether to buy in Cupertino now versus waiting for The Rise to add inventory, the honest answer is that waiting doesn't help you in 2026 or 2027. The earliest homes are still projected for 2028, and that's contingent on permitting and construction financing holding to schedule, which large Bay Area projects don't always do.
The Timeline, in Order
| Date | What Happened |
|---|---|
| November 2025 | Sand Hill Property Co. files third modification, cutting office/retail and shifting unit mix toward market-rate homes |
| February 27, 2026 | City of Cupertino approves the third modification |
| 2026 | Developer targets start of vertical (above-ground) construction |
| August 24, 2026 | City approves Modification #4 for Blocks 1 and 2, covering 493 combined homes, with no pricing or sales timeline attached |
| 2028 (earliest) | First residents could move into completed units, if the current schedule holds |
Nothing on this timeline changes the number of homes available to buy in Cupertino this year or next.
What This Means If You're Cross-Shopping Cupertino
If you're comparing Cupertino against Tri-Valley or East Bay markets, three things follow from what the data actually shows rather than what the headlines suggest.
The citywide median is not a stable benchmark right now. A quarter where more condos trade will show a lower number than a quarter dominated by larger single-family sales, even if nothing about underlying value changed. Ask what actually sold before treating a median swing as a market signal.
The Rise won't affect your near-term inventory. Whatever effect thousands of eventual new homes might have on competition for existing Cupertino properties, it isn't showing up in 2026 or 2027. Anyone telling you to wait for Vallco to loosen up the market is describing 2028 at the earliest, and that date has already moved once.
The lower entry point in Cupertino exists, but it's not evenly distributed. The City Center segment shows meaningfully lower prices than the citywide figure suggests, which matters if a smaller, newer condo fits your plans better than an older single-family home on a larger lot. That's a genuinely different product and a genuinely different price tier, not a discount on the same house.
A Few Questions I Hear Often
Will The Rise lower home prices in Cupertino once it's built? Nobody can say that with confidence yet. The project's own scope has already shifted once, from a larger affordable-housing component to a plan weighted more heavily toward market-rate units. What effect a finished mixed-use district eventually has on surrounding property values will depend on how much of the original plan survives to completion and how the broader market looks when units actually deliver.
Can I buy a home at The Rise right now? Not yet. As of the most recent city approval in August 2026, no phase of the project has announced pricing, floor plans, HOA structure, or a sales release date. The city's own project status page is the most reliable place to track permitting milestones as they happen.
Is Cupertino's falling median price a sign that it's a better time to buy? Not on its own. The median dropped because the mix of homes selling shifted toward smaller and lower-priced properties, not because comparable homes got cheaper. Price per square foot actually moved the other direction over the same period.
Cupertino rewards a buyer who looks past the single citywide number and asks what's actually trading in the segment they care about. If you're weighing Cupertino against Danville, Dublin, San Ramon, or another Bay Area suburb and want help sorting out which comparison is fair and which one is comparing two different markets, I'm happy to walk through it with you.
Meenakshi Rathore — Let's Connect.
